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JEE Main 2021 · Chemistry · Biomolecules and Polymers · medium

The isoelectric point of glutamic acid is calculated from its pKa values: pKa1 (α-COOH) =2.19, pKa2 (side-chain COOH) =4.25 and pKa3 (NH3^+) =9.67.…

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The isoelectric point of glutamic acid is calculated from its pKa\mathrm{p}K_a values: pKa1\mathrm{p}K_{a1} (α\alpha-COOH) =2.19=2.19, pKa2\mathrm{p}K_{a2} (side-chain COOH) =4.25=4.25 and pKa3\mathrm{p}K_{a3} (NH3+\mathrm{NH_3^+}) =9.67=9.67. Its pI is
  1. A. 3.223.22
  2. B. 5.965.96
  3. C. 6.936.93
  4. D. 7.467.46
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Answer: (A) 3.223.22

Glutamic acid is an acidic amino acid. At low pH it is the cation +1+1; losing the α\alpha-COOH proton gives the neutral zwitterion (between pKa1\mathrm{p}K_{a1} and pKa2\mathrm{p}K_{a2}); losing the side-chain proton gives the −1-1 anion. The net charge is zero in the zwitterion region, so pI is the mean of the two pKa\mathrm{p}K_a values that bracket the neutral form: pI=2.19+4.252=3.22\mathrm{pI}=\dfrac{2.19+4.25}{2}=3.22. Averaging pKa1\mathrm{p}K_{a1} and pKa3\mathrm{p}K_{a3} (5.935.93) is the mistake used for neutral amino acids such as alanine.
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